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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Ernesto Mendoza | 91 | 2026-2034 | |
| 2 | Máximo Marín | 63 | 2022-2027 | |
| 3 | Manny Maldonado | 61 | 2014-2025 | |
| 4 | Bobby Turner# | 57 | 2046-2049 | |
| 5 | Ron Chapman | 55 | 2021-2027 | |
| 6 | Jesús Aguirre# | 54 | 2044-2049 | |
| 6 | Anatolio Lucci# | 54 | 2041-2049 | |
| 8 | António Ramos | 50 | 2011-2015 | |
| 9 | Pedro Martínez | 49 | 2018-2021 | |
| 10 | Lou Snyder# | 47 | 2039-2048 | |
| 10 | Martin White | 47 | 2022-2028 | |
| 12 | Javier Cervantes | 46 | 2014-2020 | |
| 12 | Clint Davis | 46 | 2010-2015 | |
| 12 | Ramón Fonseca | 46 | 2021-2027 | |
| 15 | John Drier# | 45 | 2044-2049 | |
| 15 | Teddy Peters# | 45 | 2043-2049 | |
| 17 | Quincy Robinson | 44 | 2010-2015 | |
| 17 | Octávio Serrano# | 44 | 2041-2048 | |
| 19 | Nariaki Tanaka | 43 | 2020-2024 | |
| 20 | Valke de Ruijter | 42 | 2007-2016 | |
| 20 | Ryan García | 42 | 2032-2037 | |
| 22 | Ray Howard | 41 | 2039-2045 | |
| 22 | Joe Waters# | 41 | 2042-2049 | |
| 24 | Dave Cardona# | 40 | 2044-2049 | |
| 24 | Phil Davis | 40 | 2022-2026 | |
| 24 | Pablo Reynosa# | 40 | 2044-2047 | |
| 24 | Luis Sandoval# | 40 | 2043-2049 | |
| 28 | Ivo Estima | 39 | 2010-2019 | |
| 29 | Jessie Carr# | 38 | 2042-2048 | |
| 30 | Aaron Green | 37 | 2023-2027 | |
| 30 | José López | 37 | 2013-2016 | |
| 32 | Steven England | 36 | 2022-2026 | |
| 32 | Carl Hock | 36 | 2007-2015 | |
| 32 | Eduardo Méndez | 36 | 2032-2037 | |
| 32 | Javier Toledo | 36 | 2021-2024 | |
| 32 | R.J. Watkins | 36 | 2013-2017 | |
| 37 | Juan Barrera | 35 | 2022-2024 | |
| 37 | Sebastián Cervantes | 35 | 2027-2030 | |
| 37 | Tony Fullerton | 35 | 2028-2031 | |
| 37 | Scott Kirby | 35 | 2039-2043 | |
| 37 | Hugh Lyons# | 35 | 2039-2046 | |
| 37 | Ron Martin | 35 | 2024-2027 | |
| 37 | Matt Moore# | 35 | 2042-2046 | |
| 44 | Kevin Bader | 34 | 2021-2028 | |
| 44 | Esteban Corona | 34 | 2024-2029 | |
| 44 | Tanner Morgan# | 34 | 2041-2049 | |
| 44 | Moromao Ogawa# | 34 | 2047-2049 | |
| 44 | Barrett Pritchard | 34 | 2030-2035 | |
| 49 | Jean Burrows | 33 | 2013-2017 | |
| 49 | Alberto Colón | 33 | 2031-2037 | |
| 49 | Jim Day# | 33 | 2047-2049 | |
| 49 | Edgardo González | 33 | 2010-2012 | |
| 49 | Marcos Medina | 33 | 2028-2032 | |
| 49 | Alejandro Silva# | 33 | 2041-2049 | |
| 49 | Dave Thornton# | 33 | 2044-2049 | |
| 56 | Tom Givens# | 32 | 2042-2049 | |
| 56 | Aluizio Subgua | 32 | 2012-2019 | |
| 58 | Bud Baldwin | 31 | 2023-2026 | |
| 58 | Tim Baxter# | 31 | 2046-2049 | |
| 58 | Richard Dorris | 31 | 2020-2024 | |
| 58 | Cole Jackson | 31 | 2009-2014 | |
| 58 | Steven Jones# | 31 | 2043-2049 | |
| 58 | Carlos Pérez# | 31 | 2035-2038 | |
| 58 | Jorge Rodríguez# | 31 | 2040-2043 | |
| 58 | Robert Spencer | 31 | 2007-2011 | |
| 58 | Fa-hsien Thum# | 31 | 2043-2047 | |
| 58 | Bryan Work# | 31 | 2043-2049 | |
| 68 | Jim Barnes | 30 | 2033-2036 | |
| 68 | John Carlson | 30 | 2011-2014 | |
| 68 | Ryan Evans# | 30 | 2046-2049 | |
| 68 | Lee Kelley# | 30 | 2046-2049 | |
| 68 | Dan Love# | 30 | 2041-2047 | |
| 68 | Curt Morton# | 30 | 2042-2049 | |
| 68 | Héctor Ramos | 30 | 2034-2041 | |
| 68 | Steve Spencer# | 30 | 2044-2049 | |
| 68 | Chris Tatum# | 30 | 2043-2049 | |
| 68 | León Varela | 30 | 2032-2034 | |
| 78 | Luka Agatov | 29 | 2008-2019 | |
| 78 | Jeffery Barker | 29 | 2008-2016 | |
| 78 | Alfredo Bermúdez | 29 | 2008-2017 | |
| 78 | Ken Cobb | 29 | 2038-2047 | |
| 78 | John Cowley# | 29 | 2041-2044 | |
| 78 | Júlio Cruz# | 29 | 2042-2047 | |
| 78 | Manuel Gil | 29 | 2024-2028 | |
| 78 | Kevin Harris | 29 | 2031-2037 | |
| 78 | Troy Hensley | 29 | 2009-2011 | |
| 78 | Cooper Morgan# | 29 | 2040-2047 | |
| 78 | Andrew Price# | 29 | 2040-2045 | |
| 78 | José Pérez | 29 | 2024-2026 | |
| 78 | Henry Reed | 29 | 2033-2038 | |
| 78 | Robert Reeves | 29 | 2014-2017 | |
| 92 | Tony Atlas# | 28 | 2046-2049 | |
| 92 | Dan Brooks# | 28 | 2040-2042 | |
| 92 | José Gómez# | 28 | 2042-2049 | |
| 92 | Carlos Hernández# | 28 | 2045-2049 | |
| 92 | Bill Nealon | 28 | 2037-2043 | |
| 92 | Martín Reyes | 28 | 2017-2021 | |
| 92 | Juan Rico# | 28 | 2046-2049 | |
| 92 | Andrés Rivera | 28 | 2019-2023 | |
| 100 | Steven Brooks | 27 | 2043-2048 |
